79669-49-1Relevant articles and documents
METHOD FOR PRODUCING 5-BROMO-2-ALKYLBENZOIC ACID
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Paragraph 0068-0070; 0079-0082, (2021/09/03)
PROBLEM TO BE SOLVED: To provide a method for producing 5-bromo-2-alkylbenzoic acid, which is useful as a synthetic intermediate of a drug substance such as an antidiabetic, in an industrially inexpensive and efficient manner. SOLUTION: The present disclosure provides a method for producing 5-bromo-2-alkylbenzoic acid by bringing 2-alkylbenzoic acid and bromine into contact with each other, in the presence of sulfuric acid. Particularly if 2-alkylbenzoic acid is 2-methylbenzoic acid, the inventive production method enables efficient production of 5-bromo-2-methylbenzoic acid to be a raw material for producing canagliflozin, one of antidiabetics. SELECTED DRAWING: None COPYRIGHT: (C)2021,JPOandINPIT
Synthesis and evaluation of a novel series of 6-bromo-1-cyclopentyl-1H-indazole-4-carboxylic acid-substituted amide derivatives as anticancer, antiangiogenic, and antioxidant agents
Sawant, Ajay S.,Kamble, Sonali S.,Pisal, Parshuram M.,Meshram, Rohan J.,Sawant, Sanjay S.,Kamble, Vilas A.,Kamble, Vinod T.,Gacche, Rajesh N.
, p. 17 - 32 (2019/11/14)
A series of novel indazole derivatives has been synthesized and evaluated for anticancer, antiangiogenic, and antioxidant activities. The capability of the synthesized compounds 11a–x to hinder the viability of three human cancer cells lines, HEP3BPN 11 (liver), MDA 453 (breast), and HL 60 (leukemia), were assessed by using the 3-(4,5-dimethylthiazol-2-yl)-2,5-diphenyltetrazolium bromide (MTT) reduction assay. Among the compounds 11a–x screened, 11c and 11d showed the higher inhibitory activity on the viability of HEP3BPN 11 (liver), when compared with the standard methotrexate. These compounds were further tested to evaluate their potential to inhibit the proangiogenic cytokines associated with tumor development. Compound 11c was found to be a potent antiangiogenic agent against TNFα, VEGF, and EGF, whereas 11d showed potent antiangiogenic activity against TNFα, VEGF, IGF1, TGFb, and leptin inhibition. All the compounds 11a–x were screened for their antioxidant activities using 2,2-diphenyl-1-picryl hydrazine (DPPH), hydroxyl (OH), and superoxide radical (SOR) scavenging activity. Compounds 11n, 11p, 11q, and 11v have shown significant OH radical scavenging activities, also compounds 11c, 11h, and 11k were found to have a DPPH radical scavenging activity and compounds 11a and 11m exhibited better SOR scavenging activity when compared with the reference compound ascorbic acid. In silico molecular docking analysis revealed important structural insights behind observed anti TNFα effect by present indazole compounds.
Synthesis, computational, and spectroscopic analysis of tunable highly fluorescent BN-1,2-azaborine derivatives containing the N-BOH moiety
Saint-Louis, Carl Jacky,Shavnore, Renée N.,McClinton, Caleb D. C.,Wilson, Julie A.,Magill, Lacey L.,Brown, Breanna M.,Lamb, Robert W.,Webster, Charles Edwin,Schrock, Alan K.,Huggins, Michael T.
, p. 10172 - 10183 (2017/12/26)
Nine new polycyclic aromatic BN-1,2-azaborine analogues containing the N-BOH moiety were synthesized using a convenient two-step, one-pot procedure. Characterization of the prepared compounds show the luminescence wavelength and the quantum yields of the azaborines were tunable by controlling the power and location of the donor and acceptor substituents on the chromophore. UV-visible spectroscopy and density functional theory (DFT) computations revealed that the addition of electron-donating moieties to the isoindolinone hemisphere raised the energy of the HOMO, resulting in the reduction of the HOMO-LUMO gap. The addition of an electron-accepting moiety to the isoindolinone hemisphere and an electron-donating group to the boronic acid hemisphere decreased the HOMO-LUMO gap considerably, leading to emission properties from partial intramolecular charge transfer (ICT) states. The combined effect of an acceptor on the isoindolinone side and a donor on the boronic acid side (strong acceptor-π-donor) gave the most red-shifted absorption. The polycyclic aromatic BN-1,2-azaborines emitted strong fluorescence in solution and in the solid-state with the largest red-shifted emission at 640 nm and a Stokes shift of Δλ = 218 nm, or Δν = 8070 cm-1.
Process for synthesizing card Geleg only (by machine translation)
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, (2016/12/01)
The invention discloses a process for synthesizing card Geleg only, in order to 2?Methyl benzoic acid as starting material, use of improvised catalyst, reaction to produce the iodine iodate a in the middle, or in 2?Methyl benzoic acid as starting material, the metal reagent and under the action of catalyst, by adding liquid bromine, synthetic intermediates b; optionally intermediate one or intermediate two acylation reaction with thionyl chloride, to Friedel-crafts reaction produce intermediate three; in order to ALPHA?D?Glucose as raw material, with the reaction protection of all hydroxyl after pivalyl chloride, and then with zinc bromide, trimethyl silane reaction produce intermediate four; three intermediate the intermediate body, connecting delivery into intermediate five; finally under acidic conditions to remove the acyl special fifth heavenly stem, produce the target compound. card Geleg only of the present invention new process for the synthesis of high yield, mild condition, safety and reliability, is suitable for industrial production, raw material is cheap and easy to obtain, it is beneficial to control the production cost. (by machine translation)
Series of structural and functional models for the ES (enzyme-substrate) complex of the Co(II)-containing quercetin 2,3-dioxygenase
Sun, Ying-Ji,Huang, Qian-Qian,Zhang, Jian-Jun
supporting information, p. 2932 - 2942 (2014/04/03)
A series of mononuclear CoII-flavonolate complexes [Co IILR(fla)] (LRH = 2-{[bis(pyridin-2-ylmethyl) amino]methyl}-p/m-R-benzoic acid; R = p-OMe (1), p-Me (2), m-Br (4), and m-NO2 (5); fla = flavonolate) were designed and synthesized as structural and functional models for the ES (enzyme-substrate) complexes to mimic the active site of the Co(II)-containing quercetin 2,3-dioxygenase (Co-2,3-QD). The metal center Co(II) ion in each complex shows a similar distorted octahedral geometry. The model complexes display high enzyme-type dioxygenation reactivity (oxidative O-heterocyclic ring opening of the coordinated substrate flavonolate) at low temperature, presumably due to the attached carboxylate group in the ligands. The reactivity exhibits a substituent group dependent order of -OMe (1) > -Me (2) > -H (3)14b > -Br (4) > -NO2 (5), and the Hammett plot is linear (ρ = -0.78). This can be explained as the electronic nature of the substituent group in the ligands may influence the conformation and redox potential of the bound flavonolate and finally bring different reactivity. The structures, properties, and reactivity of the model complexes show some dependence on the substituent group in the supporting model ligands, and there is some relationship among them. This study is the first example of a series of structural and functional ES models of Co-2,3-QD, with focus on the effects of the electronic nature of substituted groups and the carboxylate group of the ligands to the dioxygenation reactivity, that will provide important insights into the structure-property-reactivity relationship and the catalytic role of Co-2,3-QD.
Synthesis and characterization of π-extended porphyrins as potential precursors for the formation of columnar mesophases: Design principles for columnar mesophases need revision?
Herzog, Beat,Neier, Reinhard
experimental part, p. 29 - 44 (2011/06/18)
A series of meso-a bridged extended porphyrins substituted with long aliphatic chains were synthesized and fully characterized. Two different synthetic strategies were tested to obtain the target structures. The synthetic steps were optimized in order to obtain scalable routes for the production of sufficient quantities of η-extended porphyrins for material science studies. The porphyrins were obtained either as free bases or complexed with Ni II or CuII. UV-Vis spectroscopy and polarized light microscopy was used for the analysis of the material properties of the η-extended porphyrins. The results obtained with our compounds are not compatible with the results reported in the literature. ARKAT-USA, Inc.
INHIBITORS OF DIACYLGLYCEROL ACYL TRANSFERASE
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Example 1, (2011/07/30)
The present invention relates to heterocyclic compounds in all their stereoisomeric and tautomeric forms; and their pharmaceutically acceptable salts, pharmaceutically acceptable solvates and pharmaceutically acceptable polymorphs. The invention also relates to processes for the manufacture of the heterocyclic compounds and to pharmaceutical compositions containing them. The said compounds and their pharmaceutical compositions are useful in the prevention and treatment of diseases or disorders mediated by diacylglycerol acyltransferase (DGAT), particularly DGAT1. The present invention further provides a method of treatment of such diseases or disorders by administering a therapeutically effective amount of said compounds or their pharmaceutical compositions, to a mammal in need thereof.
Synthesis of N-methyl-6-heterocyclic-1-oxoisoindoline derivatives by microwave assisted buchwald-hartwig amination
Kishor Kumar,Vijay Kumar,Naik, Nagaraja
scheme or table, p. 1108 - 1113 (2012/06/15)
An rapid and efficient microwave assisted Pd(II) catalyzed protocol for the preparation of N-methyl-6-heterocyclic-1-oxoisoindoline derivatives by Buchwald-Hartwig amination with an overall yield 68-85% has been described.
MODULATORS OF ATP-BINDING CASSETTE-TRANSPORTERS
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Page/Page column 55, (2009/06/27)
Compounds of the present invention, and pharmaceutically acceptable compositions thereof, are useful as modulators of ATP-Binding Cassette (""ABC"") transporters or fragments thereof, including Cystic Fibrosis Transmembrane Conductance Regulator (""CFTR""). The present invention also relates to methods of treating ABC transporter mediated diseases using compounds of the present invention.
Synthetic strategies to derivatizable triphenylamines displaying high two-photon absorption
Lartia, Remy,Allain, Clemence,Bordeau, Guillaume,Schmidt, Falk,Fiorini-Debuisschert, Celine,Charra, Fabrice,Teulade-Fichou, Marie-Paule
, p. 1732 - 1744 (2008/09/18)
(Chemical Equation Presented) A versatile synthetic strategy to access a set of highly fluorescent π-conjugated triphenylamines bearing a functional linker at various positions on one phenyl ring is described. These compounds were designed for large two-photon absorption (2PA) and in particular for labeling of biomolecules. The monoderivatized trisformylated or trisiodinated intermediates described herein allow introduction of a large variety of electron-withdrawing groups required for large 2PA as well as a panel of chemical functions suitable for coupling to biomolecules. The monoderivatized three-branched compounds and in particular the benzothiazole (TP-3Bz) series show remarkable linear (high extinction coefficients and high quantum yield) and nonlinear (high 2-photon cross sections) optical properties. Interestingly the presence of functional side chains does not disturb the two-photon absorption. Finally, monoderivatized two-branched derivatives also appear to be valuable candidates. Altogether the good optical properties of the new derivatizable π-conjugated TPA combined with their small size and their compatibility with bioconjugation protocols suggest that they represent a new chemical class of labels potentially applicable for the tracking of biomolecules using two-photon scanning microscopy.
